NP-MRD: Showing NP-Card for [(1s,2r,3r,4s,5r,6s,8r,9s,10s,13s,16r,17r,18s)-4-(benzyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate (NP0186487)

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Record Information

Version

2.0

Created at

2022-09-04 02:21:30 UTC

Updated at

2022-09-04 02:21:30 UTC

NP-MRD ID

NP0186487

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s,2r,3r,4s,5r,6s,8r,9s,10s,13s,16r,17r,18s)-4-(benzyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate

Description

[(1S,2R,3R,4S,5R,6S,8R,9S,10S,13S,16R,17R,18S)-4-(benzyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom. [(1s,2r,3r,4s,5r,6s,8r,9s,10s,13s,16r,17r,18s)-4-(benzyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate is found in Consolida ajacis. Based on a literature review very few articles have been published on [(1S,2R,3R,4S,5R,6S,8R,9S,10S,13S,16R,17R,18S)-4-(benzyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309042204212D          

 55 63  0  0  1  0            999 V2000
   -0.7670    1.6555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5114    0.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -0.0965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6588   -0.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2975   -1.5822    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9580   -2.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5260   -2.7891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3557   -2.8975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9262   -2.2631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5491   -3.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0553   -4.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3807   -5.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2000   -5.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6938   -4.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3683   -3.8050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8621   -3.1442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6871   -3.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3565   -3.6734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9525   -2.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2916   -1.8802    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3026   -1.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6177   -2.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9896   -1.6281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0658   -2.4074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7386   -2.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2651   -1.9996    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3934   -2.8975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7318   -3.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0555   -1.1386    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7448   -0.1610    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3214    0.0376    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4399    0.8935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3127   -0.3021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5702    0.1683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4479    0.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4024   -1.2058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2286   -0.1963    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4372    0.6579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429    0.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6610   -0.5791    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4903   -0.2613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0298    0.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3846   -1.4246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5644   -2.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8378   -1.5663    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3108   -1.0284    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9548   -1.7699    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7234   -2.2230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4671   -2.6573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6040   -3.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3593   -3.8093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4495   -4.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7843   -5.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0291   -4.7855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9389   -3.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  2  0  0  0  0
  5 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30  3  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 36 33  1  1  0  0  0
  5 36  1  0  0  0  0
 29 36  1  0  0  0  0
 31 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  6  0  0  0
 41 42  1  0  0  0  0
 40 43  1  0  0  0  0
 43 44  1  1  0  0  0
 45 44  1  1  0  0  0
 29 45  1  0  0  0  0
 46 45  1  1  0  0  0
 37 46  1  0  0  0  0
 46 47  1  0  0  0  0
 43 47  1  0  0  0  0
 47 48  1  6  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 54 55  2  0  0  0  0
 50 55  1  0  0  0  0
M  END


  Mrv1652309042204212D          

 55 63  0  0  1  0            999 V2000
   -0.7670    1.6555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5114    0.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -0.0965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6588   -0.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2975   -1.5822    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9580   -2.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5260   -2.7891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3557   -2.8975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9262   -2.2631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5491   -3.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0553   -4.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3807   -5.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2000   -5.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6938   -4.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3683   -3.8050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8621   -3.1442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6871   -3.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3565   -3.6734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9525   -2.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2916   -1.8802    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3026   -1.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6177   -2.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9896   -1.6281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0658   -2.4074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7386   -2.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2651   -1.9996    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3934   -2.8975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7318   -3.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0555   -1.1386    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7448   -0.1610    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3214    0.0376    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4399    0.8935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3127   -0.3021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5702    0.1683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4479    0.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4024   -1.2058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2286   -0.1963    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4372    0.6579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429    0.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6610   -0.5791    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4903   -0.2613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0298    0.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3846   -1.4246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5644   -2.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8378   -1.5663    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3108   -1.0284    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9548   -1.7699    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7234   -2.2230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4671   -2.6573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6040   -3.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3593   -3.8093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0291   -4.7855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9389   -3.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
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 34 35  1  0  0  0  0
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  5 36  1  0  0  0  0
 29 36  1  0  0  0  0
 31 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
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 40 41  1  6  0  0  0
 41 42  1  0  0  0  0
 40 43  1  0  0  0  0
 43 44  1  1  0  0  0
 45 44  1  1  0  0  0
 29 45  1  0  0  0  0
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 37 46  1  0  0  0  0
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 43 47  1  0  0  0  0
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 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
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 53 54  1  0  0  0  0
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 50 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0186487

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@]2(COC(=O)C3=CC=CC=C3N3C(=O)C[C@H](C)C3=O)CC[C@@H](OC)[C@@]34[C@@H]5C[C@H]6[C@H](OCC7=CC=CC=C7)[C@@H]5[C@](O)(C[C@@H]6OC)[C@@](O)([C@@H](OC)[C@H]23)[C@@H]14

> <INCHI_IDENTIFIER>
InChI=1S/C43H54N2O10/c1-6-44-22-40(23-55-38(48)26-14-10-11-15-29(26)45-32(46)18-24(2)37(45)47)17-16-31(52-4)42-28-19-27-30(51-3)20-41(49,43(50,39(42)44)36(53-5)35(40)42)33(28)34(27)54-21-25-12-8-7-9-13-25/h7-15,24,27-28,30-31,33-36,39,49-50H,6,16-23H2,1-5H3/t24-,27+,28+,30-,31+,33+,34-,35+,36-,39-,40-,41+,42-,43+/m0/s1

> <INCHI_KEY>
QGSCOUYMMQMFSA-OCMICNTHSA-N

> <FORMULA>
C43H54N2O10

> <MOLECULAR_WEIGHT>
758.909

> <EXACT_MASS>
758.377845947

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
109

> <JCHEM_AVERAGE_POLARIZABILITY>
82.5021216843482

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,2R,3R,4S,5R,6S,8R,9S,10S,13S,16R,17R,18S)-4-(benzyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate

> <JCHEM_LOGP>
2.2426662586666657

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.99399012690806

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.219118108211104

> <JCHEM_PKA_STRONGEST_BASIC>
9.65828479883446

> <JCHEM_POLAR_SURFACE_AREA>
144.3

> <JCHEM_REFRACTIVITY>
200.22179999999992

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2R,3R,4S,5R,6S,8R,9S,10S,13S,16R,17R,18S)-4-(benzyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.432   3.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.955   1.525   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.182  -0.180   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.230  -1.505   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.555  -2.953   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.788  -4.040   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.849  -5.206   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.397  -5.409   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.462  -4.224   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.758  -6.921   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.837  -8.155   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.444  -9.570   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.973  -9.752   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.895  -8.518   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.288  -7.103   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -7.209  -5.869   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -8.749  -5.890   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -9.999  -6.857   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -9.245  -4.432   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -8.011  -3.510   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -8.032  -1.970   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.753  -4.398   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.581  -3.039   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.123  -4.494   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.379  -4.926   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.361  -3.733   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.601  -5.409   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.233  -6.924   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.970  -2.125   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.390  -0.301   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.467   0.070   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.688   1.668   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.584  -0.564   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.064   0.314   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.703   0.713   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.751  -2.251   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.160  -0.366   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       4.550   1.228   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       5.680   0.015   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.834  -1.081   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       8.382  -0.488   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       9.389   0.762   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       6.318  -2.659   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       4.787  -3.979   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       3.431  -2.924   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       4.314  -1.920   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       5.516  -3.304   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       6.950  -4.150   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       8.339  -4.960   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       8.594  -6.491   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      10.004  -7.111   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      10.172  -8.642   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       8.931  -9.553   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       7.521  -8.933   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       7.353  -7.402   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   24   36                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   16   23                                                  
CONECT   23   22                                                            
CONECT   24    5   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30   36   45                                             
CONECT   30   29    3   31                                                  
CONECT   31   30   32   33   37                                             
CONECT   32   31                                                            
CONECT   33   31   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33    5   29                                                  
CONECT   37   31   38   39   46                                             
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   41   43                                                  
CONECT   41   40   42                                                       
CONECT   42   41                                                            
CONECT   43   40   44   47                                                  
CONECT   44   43   45                                                       
CONECT   45   44   29   46                                                  
CONECT   46   45   37   47                                                  
CONECT   47   46   43   48                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51   55                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   50                                                       
MASTER        0    0    0    0    0    0    0    0   55    0  126    0
END

View in JSmol

Synonyms

Value	Source
[(1S,2R,3R,4S,5R,6S,8R,9S,10S,13S,16R,17R,18S)-4-(Benzyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1,.0,.0,.0,]nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoic acid	Generator

Chemical Formula

C₄₃H₅₄N₂O₁₀

Average Mass

758.9090 Da

Monoisotopic Mass

758.37785 Da

IUPAC Name

[(1S,2R,3R,4S,5R,6S,8R,9S,10S,13S,16R,17R,18S)-4-(benzyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCN1C[C@]2(COC(=O)C3=CC=CC=C3N3C(=O)C[C@H](C)C3=O)CC[C@@H](OC)[C@@]34[C@@H]5C[C@H]6[C@H](OCC7=CC=CC=C7)[C@@H]5[C@](O)(C[C@@H]6OC)[C@@](O)([C@@H](OC)[C@H]23)[C@@H]14

InChI Identifier

InChI=1S/C43H54N2O10/c1-6-44-22-40(23-55-38(48)26-14-10-11-15-29(26)45-32(46)18-24(2)37(45)47)17-16-31(52-4)42-28-19-27-30(51-3)20-41(49,43(50,39(42)44)36(53-5)35(40)42)33(28)34(27)54-21-25-12-8-7-9-13-25/h7-15,24,27-28,30-31,33-36,39,49-50H,6,16-23H2,1-5H3/t24-,27+,28+,30-,31+,33+,34-,35+,36-,39-,40-,41+,42-,43+/m0/s1

InChI Key

QGSCOUYMMQMFSA-OCMICNTHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Consolida ajacis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Aconitane-type diterpenoid alkaloids

Alternative Parents

Substituents

Aconitane-type diterpenoid alkaloid
Acylaminobenzoic acid or derivatives
1-phenylpyrrolidine
Benzoate ester
Quinolidine
Benzoic acid or derivatives
Benzylether
Alkaloid or derivatives
Benzoyl
Azepane
Monocyclic benzene moiety
Carboxylic acid imide, n-substituted
Piperidine
Pyrrolidone
2-pyrrolidone
Benzenoid
Tertiary alcohol
Pyrrolidine
Pyrrole
Carboxylic acid imide
Cyclic alcohol
Dicarboximide
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
1,2-aminoalcohol
Carboxylic acid ester
Lactam
1,2-diol
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Dialkyl ether
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Amine
Alcohol
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.24	ChemAxon
pKa (Strongest Acidic)	12.22	ChemAxon
pKa (Strongest Basic)	9.66	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	144.3 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	200.22 m³·mol⁻¹	ChemAxon
Polarizability	82.5 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162892411

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1s,2r,3r,4s,5r,6s,8r,9s,10s,13s,16r,17r,18s)-4-(benzyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate (NP0186487)

MOL for NP0186487 ([(1s,2r,3r,4s,5r,6s,8r,9s,10s,13s,16r,17r,18s)-4-(benzyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate)

3D MOL for NP0186487 ([(1s,2r,3r,4s,5r,6s,8r,9s,10s,13s,16r,17r,18s)-4-(benzyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate)

3D SDF for NP0186487 ([(1s,2r,3r,4s,5r,6s,8r,9s,10s,13s,16r,17r,18s)-4-(benzyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate)

3D-SDF for NP0186487 ([(1s,2r,3r,4s,5r,6s,8r,9s,10s,13s,16r,17r,18s)-4-(benzyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate)

PDB for NP0186487 ([(1s,2r,3r,4s,5r,6s,8r,9s,10s,13s,16r,17r,18s)-4-(benzyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate)

3D PDB for NP0186487 ([(1s,2r,3r,4s,5r,6s,8r,9s,10s,13s,16r,17r,18s)-4-(benzyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate)

SMILES for NP0186487 ([(1s,2r,3r,4s,5r,6s,8r,9s,10s,13s,16r,17r,18s)-4-(benzyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate)

INCHI for NP0186487 ([(1s,2r,3r,4s,5r,6s,8r,9s,10s,13s,16r,17r,18s)-4-(benzyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate)

Structure for NP0186487 ([(1s,2r,3r,4s,5r,6s,8r,9s,10s,13s,16r,17r,18s)-4-(benzyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate)

3D Structure for NP0186487 ([(1s,2r,3r,4s,5r,6s,8r,9s,10s,13s,16r,17r,18s)-4-(benzyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate)